Water → 5-bromo-1-(4-nitro-benzyl)-1H-indole-2-carboxylic acid ethyl ester

HRID 342803Notes

Reaction equation

HRID 342803 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Br:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2].[H-].[Na+].[N+:18]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1)([O-:20])=[O:19].O>CS(C)=O.CCCCCC>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:25][C:24]2[CH:27]=[CH:28][C:21]([N+:18]([O-:20])=[O:19])=[CH:22][CH:23]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Br:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 660114-Nitrobenzyl bromideHCID 259091Ethyl 5-Bromoindole-2-carboxylate

Product 1

HCID 543953975-bromo-1-(4-nitro-benzyl)-1H-indole-2-carboxylic acid ethyl esterYield 81.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8058HexaneSolvent

Procedure

To a stirring solution of 5-bromo-1H-indole-2-carboxylic acid ethyl ester (2.68 g, 10 mmol, ICN) in dry dimethylsulfoxide (42 ml) at room temperature under nitrogen was added sodium hydride (264 mg, 11 mmol) as a slurry in hexane in four equal portions over about ten minutes. 4-Nitrobenzyl bromide (2.16 g, 10 mmol) in dry dimethylsulfoxide (12 ml) was added dropwise over about five minutes. The mixture was stirred 2 hours, poured into water (50 ml) and extracted with ethyl acetate. The solution was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was flash chromatographed on silica gel (110 g, methylene chloride) to give the title compound (3.28 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe solution was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customchromatographed on silica gel (110 g, methylene chloride)

Sources & evidence

ORD record
ord-dad90ed026b1434987b5f2506aa3f8cd
Source dataset
uspto-grants-1999_01
Patent number
US05859044

Reaction notes

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